I own two houses in Portland, OR, one of which I have lived in the last 8 years- but we Just moved far away. I am debating whether to continue to rent them or to sell one or both of them. From the calculators I've looked at, it seems like it makes more sense very-long-term to hold on, but I'd love other's thoughts/resources (I'm not passionate about passing on as-much-as-possible to my kids when I die).

From a blog post on this site about when to sell, one of the factors was when things have appreciated more than the rents in the area- but I wasn't sure when it was 'enough.' I also saw a blog post by the Financial Samurai that said if he could sell a rental for more than 100x the monthly rent, he should... but I wasn't sure if others liked that as a general rule?

Some info:

-The 'investment property' is worth ~$650K and is paid off. We bought it for $225K and spent another ~$80K on improvements. Rents currently for $2495/mo. (It could be rented for more, maybe $3000/mo, but I'm only comfortable charging so much on principle. However, for some reason I wouldn't feel badly at all selling to the highest bidder)

-The other is worth maybe 525, owe $240K on it at 2.85%, and am currently renting it for 2250. Bought it for $230K.

-Both homes have new windows, kitchens, baths, flooring, electric, solar, landscaping, you name it, with custom tile and woodwork. Even though they don't need major projects or much maintenance, now that we're parents and don't live there, it's still annoying when things come up.

-There is more rental income potential because of the large yards, by having a tiny house/renting out the garage/etc.

What I'm worried about:

-We couldn't help but improve the houses a ton, and part of us feels like it's a 'waste' to just have them rented, as it will put wear and tear on them until we do want to sell... So we're wondering if we'd get more by selling when they look great/fresh?

-We have 3 years, or until we buy another house, for one of them to be considered a 'rental property' and subject to those capital gains. And, we'll probably want to buy another house before then.

We don't need the cash from the sale to buy another house, though it could be helpful.

Excited to hear your thoughts!

Portland, Oregon

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